Introducing: Dear Sheilah

Kejal Macdonald

In the winter of 2013, I was hand plucked by Lady Justice to sit alongside 11 of my peers for 4 weeks in a wood-paneled Los Angeles courthouse, ultimately determining the fate of one man. Serving on a jury for a murder trial wasn't exactly a one-month vacation, but I felt strangely honored to serve my civic duty. Plus, that's how I met Sheilah.

On the first day of selection (voir dire for you Frenchies), 100 potential jurors shuffled around quietly in the hallway, silently practicing their excuses and waiting to be called in by the judge. One voice dared to raise above a whisper - an older woman cracking jokes and striking up conversations. I gravitated to her.

Sheilah and I ate lunch together that day, and every day for the next month. I was enamored by how wise and hilarious she was. Best of all, no topic was off limits - love, heartbreak, marriage, divorce, family, sex, money, art, purpose - Sheilah's lived like 18 lives, and is working on her 19th.

Three years (and a cross-country move + baby) later, I'm still turning to Sheilah for guidance. She's my human equivalent of a magic 8 ball. She's also major hashtag goals when it comes to aging defiantly. She simultaneously gives zero fucks, while giving all the right fucks.

I can no longer on my good conscience keep Sheilah's wisdom all to myself. The time has come for my insightful sage to get her own stage as our official resident Icon advice giver. Our version of Dear Abby, if Abby looked like a Real Housewife and toked up like Cheech and Chong.

So without further ado, allow me to introduce my good friend Sheilah (and her Yorkie Max bc she doesn't go anywhere without him) tackling our first three reader conundrums.

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Dear Sheilah, Aging can feel daunting in a society that largely ignores us ladies as we get older. How do you stay feeling sexy in your late 60s? Yours,Gracing Agefully

Dear Gracing Agefully,If you feel ignored, you will be ignored.You must first find a way to appreciate all you have accomplished in your years on this earth. There is only one you! Having said all that, here is what I would like you to do:Take off those parachute undies, lift up that up that saggy bra, and for goodness sake take off those elastic waist pants. They always make our butts look flat.Now my dear G.A., I want you to tell the Universe with all your body and soul “I want to get laid!”Imagine yourself in the arms of someone you remember. That one guy or gal that got your juices flowing.Come on, there had to be someone.Yes I know you’re dried up, the walls of your vag are paper thin, and your Gynecologist can’t even get a swab in you, but don’t get discouraged.Every time you go out, show some swag. Have that come-hither look. (I know you remember that look.)I want you to feel it. Live it. Taste it. Show yourself and the world how sexy the one and only G.A. is andbefore you know it, you’ll be asking for a bigger swab!

Xo,Sheilah

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Dear Sheilah,How has your relationship to fear changed over the years? Do you feel more liberated with each passing year?With Love,Red

Dear Red,What an interesting question.Fear to me always meant the unknown. As the years have flown by, I’ve learned that fear can be a blessing. It can make you face yourself, which is the scariest fear of all. I have faced myself and realized the only thing I’m afraid of now is falling!Liberation can mean different things to many people. For my Daughter, it was when she got her hysterectomy. For me, feeling liberated was when I realized that my thoughts became things. What I really wanted and focused on happened whether I wanted it or not. Knowing that, I started to create my own world. I am creating the life I choose to live. For me, not anyone else. How liberating is that?! Now that you know the secret Red, think and grow happy.

Xo,Sheilah

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Dear Sheilah,I am a single woman in my late twenties (just turned 29, eep!) I have been single for three years now and live alone in NYC.I have always wanted a family, or at least a strong relationship, as I feel very happy when I am close with people. However, dating has proved very challenging for me. In the past year I have been actively going on dates, hoping to meet someone and start a relationship. But all of the men I have met only want casual sex relationships, or they break up with me after a couple of months, just when I start to feel like we are developing a bond. I keep telling myself you have to meet a lot of people before you find someone you really click with, but the rejection has really started to chip away at my self-esteem. Sincerely,Lonesome in NYC

Dear Lonesome,First of all, can you send the numbers of these men to Gracing Agefully?Oh my little Lonesome, relationships are not all that they are cracked up to be. Trust me, I’ve been married 3 times. But we’re not talking about me here. You have heard what I’m about to tell you more times then you can count, so better add another hand. What you are craving is an inside job. You are all you need. What if no one ever came into your life? (Put the pills down.) Would you want to feel empty and alone for another 60 years with 29 cats?I think not.Finding your soulmate (I used that term for your benefit) is not a numbers game. It’s an energy game.Ever passed some guy on an escalator and your eyes met? For the fraction of a second you had a tingle connection, an energy exchange. You were on the same wave length. Get what I’m saying? Don’t waste anymore time feeling rejected. Start feeling the energy of the man who is trying to find you. Don’t worry about how it’s going to happen or when. Just know that he’s on his way.From this moment on I will call you Looking Forward To Each New Day, because you never know what exciting things are about to happen. Or maybe I’ll just call you Lucky.

Xo,Sheilah

~* Trying to figure out the meaning of life? In need of advice? Have any burning questions for Sheilah? Send her your Qs: dearsheilah@iconundies.com *~